AI Article Synopsis
- Researchers are exploring ways to modify unprotected glycosides without using protecting groups, focusing on site-selective oxidation methods.
- By treating the resulting trityl hydrazone with butyl hypochlorite and a hydrogen atom donor, they successfully introduce a chloride substituent to various mono- and disaccharides.
- This method allows for controlled stereoselectivity and introduces a new geminal dichlorination reaction, presenting a more efficient approach compared to traditional methods that often result in overchlorination.
Article Abstract
To circumvent protecting groups, the site-selective modification of unprotected glycosides is intensively studied. We show that site-selective oxidation, followed by treatment of the corresponding trityl hydrazone with butyl hypochlorite and a H atom donor provides an effective way to introduce a chloride substituent in a variety of mono- and disaccharides. The stereoselectivity can be steered, and a new geminal dichlorination reaction is described as well. This strategy challenges existing methods that lead to overchlorination.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490796 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.2c01992 | DOI Listing |
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